Fred Van Winkle is an old man who fell asleep in 1929 and only woke up many decades later in 1989. He is named after Rip Van Winkle, the protagonist of a story who himself falls asleep for an extended period of time.

In The Super Mario Bros. Super Show! live-action segment "Fred Van Winkle", Fred wakes up inside Mario Brothers Plumbing as Mario and Luigi are attempting to fix their furnace. He thinks that the two of them seem nice, and invites them to "23 skidoo" and "Charleston with some "hot tamales" after he finds a razor to shave his beard. Mario thinks that he is crazy, but Luigi disagrees (while also understanding his lingo) and asks Fred when fell asleep. When Fred replies "last night," he then asks what year it is. Fred promptly states that the year is 1929, which he quips was a great year for depressions. The three of them then introduce themselves to each other, and Luigi compliments Fred's beard. Luigi then begins describing all of the new technology that has appeared while Fred was sleeping, including portable computers, video games, and even indoor plumbing, and Fred is impressed by all of this. Fred then sees Mario playing on an Etch A Sketch, which he initially confuses for a computer until Mario tells him that it is a toy. He assumes that the Slinky next to it is also a toy, but Mario jokes that it is actually a phone that connects to Mars. Fred believes him and then attempts to call the planet. As Luigi tells Mario not to tell any jokes, Fred gets his beard stuck in a vacuum cleaner, which he is convinced is trying to eat him. Eventually, Mario dresses him in some of his clothes (which are too big for him, but only because he has not eaten for sixty years, according to Mario), and the two brothers then offer to take Fred outside to see all of New York. As they begin describing what they plan to see, including the Statue of Liberty and Staten Island, Fred suddenly gets tired and walks back inside the building to sleep. When Mario asks him when he wants them to wake him up, he replies 1997. He wanders off, but he is chased by Mario and Luigi when they realize that he plans to sleep for eight years.